JPH0825878B2 - 局所的メトロニダゾール製剤 - Google Patents

局所的メトロニダゾール製剤

Info

Publication number: JPH0825878B2
Authority: JP; Japan
Prior art keywords: formulation; weight; metronidazole; polymer; formulations
Prior art date: 1987-03-20
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

JP62502276A

Other languages

English (en)

Japanese (ja)

Other versions

JPH01503061A (ja

Inventor

ロバートジョンボーグマン

Original Assignee

ガルデルマエスアー

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1987-03-20

Filing date

1987-03-20

Publication date

1996-03-13

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=22202320&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=JPH0825878(B2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1987-03-20 Application filed by ガルデルマエスアー filed Critical ガルデルマエスアー

1989-10-19 Publication of JPH01503061A publication Critical patent/JPH01503061A/ja

1996-03-13 Publication of JPH0825878B2 publication Critical patent/JPH0825878B2/ja

2011-03-13 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 77
238000009472 formulation Methods 0.000 title claims abstract description 76
VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 title claims abstract description 45
229960000282 metronidazole Drugs 0.000 title claims abstract description 42
230000000699 topical effect Effects 0.000 title claims description 11
239000004615 ingredient Substances 0.000 claims abstract description 8
238000001035 drying Methods 0.000 claims abstract 3
229920000642 polymer Polymers 0.000 claims description 22
206010000496 acne Diseases 0.000 claims description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
238000002360 preparation method Methods 0.000 claims description 12
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 9
208000002874 Acne Vulgaris Diseases 0.000 claims description 8
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 8
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 claims description 8
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 claims description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical group CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 7
239000003755 preservative agent Substances 0.000 claims description 7
239000003961 penetration enhancing agent Substances 0.000 claims description 6
239000012153 distilled water Substances 0.000 claims description 5
230000001965 increasing effect Effects 0.000 claims description 5
238000000034 method Methods 0.000 claims description 5
230000002335 preservative effect Effects 0.000 claims description 5
229920002554 vinyl polymer Polymers 0.000 claims description 5
229920002125 Sokalan® Polymers 0.000 claims description 4
230000002378 acidificating effect Effects 0.000 claims description 4
238000001879 gelation Methods 0.000 claims description 4
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 claims description 4
239000004292 methyl p-hydroxybenzoate Substances 0.000 claims description 4
229960002216 methylparaben Drugs 0.000 claims description 4
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 claims description 4
239000004405 propyl p-hydroxybenzoate Substances 0.000 claims description 4
229960003415 propylparaben Drugs 0.000 claims description 4
239000003125 aqueous solvent Substances 0.000 claims description 3
239000000499 gel Substances 0.000 abstract description 25
230000000694 effects Effects 0.000 abstract description 18
201000004624 Dermatitis Diseases 0.000 abstract description 8
239000012049 topical pharmaceutical composition Substances 0.000 abstract description 8
239000003814 drug Substances 0.000 abstract description 7
229940079593 drug Drugs 0.000 abstract description 5
241001303601 Rosacea Species 0.000 abstract description 2
239000002085 irritant Substances 0.000 abstract description 2
231100000021 irritant Toxicity 0.000 abstract description 2
201000004700 rosacea Diseases 0.000 abstract description 2
239000008186 active pharmaceutical agent Substances 0.000 description 28
229940088679 drug related substance Drugs 0.000 description 28
229940068196 placebo Drugs 0.000 description 23
239000000902 placebo Substances 0.000 description 23
238000011282 treatment Methods 0.000 description 23
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
239000000546 pharmaceutical excipient Substances 0.000 description 15
210000003491 skin Anatomy 0.000 description 12
239000012907 medicinal substance Substances 0.000 description 10
230000001225 therapeutic effect Effects 0.000 description 9
239000007864 aqueous solution Substances 0.000 description 8
208000017520 skin disease Diseases 0.000 description 7
239000000126 substance Substances 0.000 description 7
206010015150 Erythema Diseases 0.000 description 6
231100000321 erythema Toxicity 0.000 description 6
230000035515 penetration Effects 0.000 description 6
239000003921 oil Substances 0.000 description 5
239000006071 cream Substances 0.000 description 4
201000010099 disease Diseases 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
208000027866 inflammatory disease Diseases 0.000 description 4
208000003251 Pruritus Diseases 0.000 description 3
239000013011 aqueous formulation Substances 0.000 description 3
210000000170 cell membrane Anatomy 0.000 description 3
230000007794 irritation Effects 0.000 description 3
208000035824 paresthesia Diseases 0.000 description 3
238000013268 sustained release Methods 0.000 description 3
239000012730 sustained-release form Substances 0.000 description 3
210000001519 tissue Anatomy 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
206010033733 Papule Diseases 0.000 description 2
206010037888 Rash pustular Diseases 0.000 description 2
230000002411 adverse Effects 0.000 description 2
230000001580 bacterial effect Effects 0.000 description 2
210000004027 cell Anatomy 0.000 description 2
238000009792 diffusion process Methods 0.000 description 2
239000003623 enhancer Substances 0.000 description 2
230000006870 function Effects 0.000 description 2
230000006872 improvement Effects 0.000 description 2
230000001939 inductive effect Effects 0.000 description 2
230000007803 itching Effects 0.000 description 2
239000012528 membrane Substances 0.000 description 2
230000000069 prophylactic effect Effects 0.000 description 2
208000029561 pustule Diseases 0.000 description 2
230000002829 reductive effect Effects 0.000 description 2
230000035807 sensation Effects 0.000 description 2
239000000243 solution Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
241000894006 Bacteria Species 0.000 description 1
208000017667 Chronic Disease Diseases 0.000 description 1
206010011985 Decubitus ulcer Diseases 0.000 description 1
208000008960 Diabetic foot Diseases 0.000 description 1
206010013786 Dry skin Diseases 0.000 description 1
241000224432 Entamoeba histolytica Species 0.000 description 1
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
208000002193 Pain Diseases 0.000 description 1
208000009675 Perioral Dermatitis Diseases 0.000 description 1
208000004210 Pressure Ulcer Diseases 0.000 description 1
240000004808 Saccharomyces cerevisiae Species 0.000 description 1
206010039793 Seborrhoeic dermatitis Diseases 0.000 description 1
206010070834 Sensitisation Diseases 0.000 description 1
206010040047 Sepsis Diseases 0.000 description 1
208000005392 Spasm Diseases 0.000 description 1
206010043189 Telangiectasia Diseases 0.000 description 1
241000224527 Trichomonas vaginalis Species 0.000 description 1
208000025865 Ulcer Diseases 0.000 description 1
206010046914 Vaginal infection Diseases 0.000 description 1
201000008100 Vaginitis Diseases 0.000 description 1
208000000558 Varicose Ulcer Diseases 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
230000003569 amebicidal effect Effects 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
125000005265 dialkylamine group Chemical group 0.000 description 1
230000009429 distress Effects 0.000 description 1
230000037336 dry skin Effects 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
229940007078 entamoeba histolytica Drugs 0.000 description 1
210000001339 epidermal cell Anatomy 0.000 description 1
210000001061 forehead Anatomy 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
239000012535 impurity Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
230000007774 longterm Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
230000005012 migration Effects 0.000 description 1
238000013508 migration Methods 0.000 description 1
230000000116 mitigating effect Effects 0.000 description 1
230000002969 morbid Effects 0.000 description 1
239000002674 ointment Substances 0.000 description 1
229940126701 oral medication Drugs 0.000 description 1
210000004789 organ system Anatomy 0.000 description 1
244000045947 parasite Species 0.000 description 1
230000008447 perception Effects 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
238000011176 pooling Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
231100000241 scar Toxicity 0.000 description 1
208000008742 seborrheic dermatitis Diseases 0.000 description 1
230000008313 sensitization Effects 0.000 description 1
230000005808 skin problem Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
230000007480 spreading Effects 0.000 description 1
238000003892 spreading Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
210000000434 stratum corneum Anatomy 0.000 description 1
230000000475 sunscreen effect Effects 0.000 description 1
239000000516 sunscreening agent Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
208000009056 telangiectasis Diseases 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
231100000397 ulcer Toxicity 0.000 description 1
241001148471 unidentified anaerobic bacterium Species 0.000 description 1
238000009827 uniform distribution Methods 0.000 description 1
230000037303 wrinkles Effects 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/74—Synthetic polymeric materials
- A61K31/765—Polymers containing oxygen
- A61K31/78—Polymers containing oxygen of acrylic acid or derivatives thereof
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
- A61K47/183—Amino acids, e.g. glycine, EDTA or aspartame
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Epidemiology (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Dermatology (AREA)
Oil, Petroleum & Natural Gas (AREA)
Bioinformatics & Cheminformatics (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Organic Chemistry (AREA)
Birds (AREA)
Inorganic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicinal Preparation (AREA)
Cosmetics (AREA)
Lubrication Of Internal Combustion Engines (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Measuring Pulse, Heart Rate, Blood Pressure Or Blood Flow (AREA)

JP62502276A 1987-03-20 1987-03-20 局所的メトロニダゾール製剤 Expired - Lifetime JPH0825878B2 (ja)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
PCT/US1987/000584 WO1988006888A1 (en)	1987-03-20	1987-03-20	Novel topical metronidazole formulations and therapeutic uses thereof

Publications (2)

Publication Number	Publication Date
JPH01503061A JPH01503061A (ja)	1989-10-19
JPH0825878B2 true JPH0825878B2 (ja)	1996-03-13

Family

ID=22202320

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP62502276A Expired - Lifetime JPH0825878B2 (ja)	1987-03-20	1987-03-20	局所的メトロニダゾール製剤

Country Status (10)

Country	Link
EP (1)	EP0305380B1 (de)
JP (1)	JPH0825878B2 (de)
KR (1)	KR950003919B1 (de)
AT (1)	ATE67667T1 (de)
AU (1)	AU610495B2 (de)
DE (1)	DE3773383D1 (de)
DK (1)	DK173844B1 (de)
FI (1)	FI88582C (de)
NO (1)	NO175883C (de)
WO (1)	WO1988006888A1 (de)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4837378A (en) *	1986-01-15	1989-06-06	Curatek Pharmaceuticals, Inc.	Topical metronidazole formulations and therapeutic uses thereof
US4859694A (en) *	1988-02-10	1989-08-22	Pavlich Frederick M	Method for treating hoof thrush and hoof rot
GB8910076D0 (en) †	1989-05-03	1989-06-21	Thackray C F Ltd	Sterilisable lubricant
SE506509C2 (sv) *	1992-04-14	1997-12-22	Bioglan Ab	Användning av imidazoler för framställning av en farmaceutisk formulering för behandling av inflammatoriska och/eller infektiösa hudsjukdomar
FR2722098B1 (fr) *	1994-07-06	1996-08-23	Cird Galderma	Nouveaux medicaments a base de metro-nidazole ou d'un melange synergetique de metronidazole et de clindamycine
GB9415290D0 (en) *	1994-07-28	1994-09-21	Zeneca Ltd	Gel formation
US5972993A (en) *	1998-03-20	1999-10-26	Avon Products, Inc.	Composition and method for treating rosacea and sensitive skin with free radical scavengers
US6468989B1 (en) *	2000-07-13	2002-10-22	Dow Pharmaceutical Sciences	Gel compositions containing metronidazole
US6387383B1 (en) *	2000-08-03	2002-05-14	Dow Pharmaceutical Sciences	Topical low-viscosity gel composition
US20060093675A1 (en) *	2004-10-29	2006-05-04	Mathew Ebmeier	Intravaginal treatment of vaginal infections with metronidazole compositions
FR2882552B1 (fr) *	2005-02-25	2008-12-26	Galderma Sa	Gel aqueux de haute stabilite a base de metronidazole et procedes pour leur preparation
US11419329B2 (en)	2010-03-12	2022-08-23	Monsanto Technology Llc	Agrochemical gel compositions
BR112013033759B1 (pt)	2011-06-28	2021-05-25	Chemo Research Sl	forma de dosagem unitária de um gel de base aquosa de metronidazol mucoadesivo e uso relacionado ao gel de base aquosa de metronidazol
CA2916002A1 (en)	2013-06-25	2014-12-31	Mission Pharmacal Company	Novel formulations for the treatment of vaginal disorders
EP3641725A1 (de)	2017-06-23	2020-04-29	The Procter and Gamble Company	Zusammensetzung und verfahren zur verbesserung der erscheinung der haut
JP2021530447A (ja)	2018-07-03	2021-11-11	ザプロクターアンドギャンブルカンパニーThe Procter & Gamble Company	皮膚状態の治療方法
WO2021247496A1 (en)	2020-06-01	2021-12-09	The Procter & Gamble Company	Method of improving penetration of a vitamin b3 compound into skin
US10959933B1 (en)	2020-06-01	2021-03-30	The Procter & Gamble Company	Low pH skin care composition and methods of using the same
JPWO2022269665A1 (de) *	2021-06-21	2022-12-29
CN115350144A (zh) *	2022-07-28	2022-11-18	苏州弘森药业股份有限公司	一种甲硝唑水凝胶及其制备方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3883661A (en) *	1971-11-09	1975-05-13	Syntex Inc	Acne treatment
US4247547A (en) *	1979-03-19	1981-01-27	Johnson & Johnson	Tretinoin in a gel vehicle for acne treatment

1987
- 1987-03-20 KR KR1019880701486A patent/KR950003919B1/ko not_active Expired - Lifetime
- 1987-03-20 JP JP62502276A patent/JPH0825878B2/ja not_active Expired - Lifetime
- 1987-03-20 DE DE8787902908T patent/DE3773383D1/de not_active Expired - Lifetime
- 1987-03-20 WO PCT/US1987/000584 patent/WO1988006888A1/en not_active Ceased
- 1987-03-20 EP EP87902908A patent/EP0305380B1/de not_active Expired - Lifetime
- 1987-03-20 AT AT87902908T patent/ATE67667T1/de not_active IP Right Cessation
- 1987-03-20 AU AU72337/87A patent/AU610495B2/en not_active Expired
1988
- 1988-11-18 DK DK198806454A patent/DK173844B1/da not_active IP Right Cessation
- 1988-11-18 FI FI885377A patent/FI88582C/fi not_active IP Right Cessation
- 1988-11-18 NO NO885172A patent/NO175883C/no unknown

Also Published As

Publication number	Publication date
EP0305380A4 (de)	1989-06-26
KR890701113A (ko)	1989-12-19
FI88582B (fi)	1993-02-26
DK645488A (da)	1989-01-19
DK173844B1 (da)	2001-12-10
NO885172L (no)	1988-11-18
ATE67667T1 (de)	1991-10-15
FI885377L (fi)	1988-11-18
NO175883C (no)	1994-12-28
AU610495B2 (en)	1991-05-23
FI885377A0 (fi)	1988-11-18
DE3773383D1 (de)	1991-10-31
WO1988006888A1 (en)	1988-09-22
EP0305380B1 (de)	1991-09-25
AU7233787A (en)	1988-10-10
KR950003919B1 (ko)	1995-04-20
NO175883B (no)	1994-09-19
JPH01503061A (ja)	1989-10-19
EP0305380A1 (de)	1989-03-08
DK645488D0 (da)	1988-11-18
NO885172D0 (no)	1988-11-18
FI88582C (fi)	1993-06-10

Legal Events

Date	Code	Title	Description
2004-03-09	R250	Receipt of annual fees	Free format text: JAPANESE INTERMEDIATE CODE: R250
2005-03-08	R250	Receipt of annual fees	Free format text: JAPANESE INTERMEDIATE CODE: R250
2006-03-07	R250	Receipt of annual fees	Free format text: JAPANESE INTERMEDIATE CODE: R250
2007-03-06	R250	Receipt of annual fees	Free format text: JAPANESE INTERMEDIATE CODE: R250
2007-03-20	EXPY	Cancellation because of completion of term

Publication	Publication Date	Title
US4837378A (en)	1989-06-06	Topical metronidazole formulations and therapeutic uses thereof
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